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4721 Lake Shore Drive, West Chesapeake
$589,500
4 Beds ⋅ 2.1 Baths ⋅ 10646764 MLS
Meticulously maintained by its original owner, this 4-bedroom home offers a spacious, thoughtfully designed layout with an extended living room, formal dining room, and a versatile bonus area that can serve as a home office, playroom, gym, or flex space. The kitchen features newer appliances, while additional updates include a tankless water heater, updated HVAC system, and recently painted exterior. The garage has been upgraded with durable speckled flooring and built-in storage for added organization. Step outside to enjoy the in-ground pool, installed three years ago, a storage shed, and a backyard that backs to a wooded area, providing a natural backdrop and added privacy. Tucked away in the Western Branch area, the neighborhood offers connections to adjacent communities with opportunities for walking, running, biking, and golf cart access. Conveniently located near shopping, dining, major highways, military installations and hospitals.

4721 Lake Shore Drive, West Chesapeake

5020 Corolla Drive, West Chesapeake
$589,000
4 Beds ⋅ 3 Baths ⋅ 10634239 MLS
Welcome to The Estates at Jolliff Landing, one of Chesapeake's premier newer communities, where this extensively upgraded 4-bedroom, 3-bath home offers a standout layout with a 420 sq ft second-level bonus space and full bath ideal for a guest suite, office, or flex room; built with nearly every major builder upgrade available, this home features upgraded LVP flooring throughout, quartz countertops, upgraded cabinetry, custom tile work, farmhouse sink, gas range, pendant light prewiring, upgraded interior doors, Trex deck, Board & Batten accents, gas fireplace, and more, with additional post-construction improvements including aluminum fencing, custom paver patio, landscaping, gutters, storage shed, and fenced backyard; located in a community known for tree-lined sidewalks, covered porches, playgrounds, sports field, bike paths, clubhouse, and resort-style pool, with convenient access to 664, shopping, and dining, this is a rare opportunity to own a highly upgraded home in Chesapeake.

5020 Corolla Drive, West Chesapeake

2243 Captiva Lane, West Chesapeake
$588,343
4 Beds ⋅ 2.1 Baths ⋅ 10595123 MLS
This traditional floor plan that offers 4 Bedrooms, 2.5 Baths, and 2400+ sq ft. Enjoy the grand design of the Primary Suite with a spacious Walk-In Closet from the Primary Bath. The dining room, kitchen & family room on the first floor allow for many entertaining evenings at home. The open floor plan provides ample space with room to stretch out. 2nd floor is spacious with 4 bedrooms & utility room. The Estates at Jolliff Landing will be a charming neighborhood boasting single-family homes with covered porches, lush gathering spaces, an assortment of yard games, a playground, water features, a sports field, bike paths, a community center, a swimming pool, and a tree-lined sidewalks. Builder is offering partial CCA & $15,000 buyer incentive (see listing agent for details) when using one of our preferred lenders. Model home open daily 12-5pm at 5023 Annapolis Drive.

2243 Captiva Lane, West Chesapeake

641 Captain Cooke Way Court, South Chesapeake
$588,000
4 Beds ⋅ 2.1 Baths ⋅ 10624267 MLS
From The Moment You Enter The Cul-De-Sac Toward The End, You'll Be Taken With The Amazing Curb Appeal This Home Offers!! From The Newer Copper Roof, Shake Style Siding And Wrap Around Porch You'll Be In L-O-V-E! This One-Owner Home Shows Pride Of Ownership Inside And Outside. Updated Throughout, This Home Offers Like New LVP Flooring And Carpet Down, 1 Large Family Room With Fireplace,1 Large Kitchen (Updated) With Wonderful Eating Area Overlooking The Spacious Backyard. Formal Living And Dining Room Is Great For Entertaining. A Laundry Room (Ceramic Tile Floor) And A Half Bath Completes The First Floor. Upstairs Are 4 Large Bedrooms With Ample Closets And 2 Full Baths. The Primary Has An Ensuite Bath That's Been Renovated And Includes A Glass Shower And"Stunning"Vanity! Outside Is A H-U-G-E Yard Enclosed With a N-E-W Vinyl($33,000.00)Fence. A Large Workshop With Electric Is Great For The Craftsman. Enjoy The Large Stamped Patio With A Retractable Awning Is Great For Outdoor Activities

641 Captain Cooke Way Court, South Chesapeake

2507 Deal's Creek Court, South Chesapeake
$587,445
4 Beds ⋅ 2.1 Baths ⋅ 10617685 MLS
The Pelican model has the perfect blend of comfort, elegance, & thoughtful design. This beautifully crafted residence features a spacious open-concept first floor with a generous living room, a gourmet kitchen with a large island, granite counter tops, a stylish dining area, & convenient mudroom/laundry room-all flowing seamlessly together for everyday living & effortless entertaining. Upstairs, retreat to the luxurious primary suite, where you'll find an oversized walk-in closet connected directly to a spa-inspired bathroom featuring LVT flooring, a soaking tub, a separate shower, a dual-sink vanity, & a private water closet. 3 additional large bedrooms & a spacious hall bath provide ample room for family or guests. One of the upstairs bedrooms is oversized & great for transforming into a second living area, playroom, or media space. This home offers so much more than just space-it’s full of character & and thoughtful details you need to see in person! Photos are of existing model.

2507 Deal's Creek Court, South Chesapeake

909 Wheatfield Way, South Chesapeake
$585,000
4 Beds ⋅ 2.1 Baths ⋅ 10644529 MLS
Welcome to 909 Wheatfield Way situated at the back of a cul-de-sac with a covered front porch. The foyer entrance opens to the arched entrance to the formal dining room with crown molding and chair rail and the formal living room. The kitchen features a Butler's Pantry, tile flooring, newer appliances with gas range, dishwasher and hood. Kitchen also features granite tops & an island with power. The great room is open to the kitchen and features a gas fireplace for relaxing get togethers. The second floor features the Primary bedroom with vaulted ceilings, dual walk-in closets, private bath with tile floors, dual sinks, garden tub & shower stall. The second floor also has 3 additional bedrooms and full bath. Situated at the back of the cul-de-sac with a large backyard, storage shed and patio for entertaining. Located with views of the 48-acre Chesapeake Arboretum protected space and just minutes from the Battlefield Blvd corridor with easy access to shopping, dining & hospitals.

909 Wheatfield Way, South Chesapeake

2718 Gum Road, West Chesapeake
$585,000
4 Beds ⋅ 2.1 Baths ⋅ 10635281 MLS
Welcome to 2718 Gum Road in Chesapeake! This spacious 4-bedroom, 2.5-bath home offers the perfect combination of comfort, functionality, and outdoor living — all with NO HOA. Inside, you’ll find granite countertops, generous living spaces, and a layout designed for both everyday living and entertaining. The large lot provides plenty of room to enjoy the outdoors and includes a swing set, storage shed, and entertaining area with pool table included. Whether you’re hosting guests, enjoying time with family, or simply looking for more space and freedom, this property delivers. Conveniently located near shopping, dining, schools, and major interstates while still offering the privacy and flexibility hard to find in today’s market. Don’t miss your opportunity to own this Chesapeake gem!

2718 Gum Road, West Chesapeake

4720 Barn Swallow Drive, West Chesapeake
$585,000
4 Beds ⋅ 2.1 Baths ⋅ 10632913 MLS
Beautiful home located in the desirable Joliff Woods subdivision. This 4 bedroom, 2.5 bath property offers approximately 2,700 square feet of living space and welcomes you with a bright, open two-story foyer filled with natural light. Situated on a generous 0.67 acre lot, the home features a large deck and spacious backyard perfect for enjoying year round gatherings with family and friends.The first floor showcases engineered hardwood flooring, a well appointed kitchen with granite countertops and stainless steel appliances, and a cozy family room with a gas fireplace. Upstairs, you’ll find four spacious bedrooms, ample closet space, and bathrooms finished with granite countertops. The primary suite includes two walk-in closets, double vanities, jetted soaking tub, and a separate stand-up shower. Additional highlights include ceiling fans throughout and TRANE HVAC units. Conveniently located with easy access to the Southside & Peninsula, military bases, shipyards, dining, and shopping.

4720 Barn Swallow Drive, West Chesapeake

517 Liverpool Court, South Chesapeake
$585,000
4 Beds ⋅ 2.1 Baths ⋅ 10632240 MLS
Fabulous opportunity to own this owner brick ranch in Cheshire Forest! It's time for the next chapter in this wonderful home's history...ready for you to make it your own! Recent upgrades include: New Roof/ Gutter Guards 2019, Kitchen remodel in 2025- to include new stove, dishwasher, vent hood, & quartz countertops. New water Heater 2025, Garage door opener 2024, HVAC replaced in 2015. Home has encapsulated crawl space, updated flooring (Beechwood and Wilsonart Laminate, in the main living area), and a large wooded backyard with lots of privacy to enjoy. Built in shelving in the FROG and the front bedroom for enhanced storage. Custom closet in Primary Bedroom, Front Bedroom & Pantry. Located in Cheshire Forest in Great Bridge, with low HOA dues that include a pool, community swim team (for a fee), tennis, volleyball, pickleball, playgrounds and a plethora of social activities for all ages, all in sought after Great Bridge Schools. Call for your private showing today!

517 Liverpool Court, South Chesapeake

501 Wessex Drive, South Chesapeake
$585,000
4 Beds ⋅ 3 Baths ⋅ 10630880 MLS
Discover this beautiful home in the heart of Great Bridge! Hardwood floors grace the foyer, dining, and great room, with cozy carpet in bedrooms. The oversized kitchen features custom leathered countertops, island, breakfast area, new 2025 refrigerator, and wood-burning fireplace. A full bath and large laundry room add convenience on the first floor. The great room boasts a pellet stove and wood-beamed ceiling. Upstairs, the spacious primary suite offers a large closet, dual vanities, and walk-in shower. Bonus room over the garage serves as a 4th bedroom. Zoned HVAC (2025). Enjoy a fully fenced backyard with deck, gazebo, and shed. Extended driveway with 50-amp RV plug—perfect for boats, RVs, or extra parking!

501 Wessex Drive, South Chesapeake

1026 Woodwind Way, South Chesapeake
$585,000
4 Beds ⋅ 2.1 Baths ⋅ 10626225 MLS
A great opportunity to call this well priced, well cared for all brick retreat in Kemp Woods your Home! Situated on a sizable cul-de-sac lot, 1026 Woodwind Way provides a great flow with 4 bedrooms, 2.5 baths and double staircases. A bright, welcoming 2-story foyer greets your guests and opens to both an office/music room and the formal dining room. The family room is the true heart and hearth of the home, opening seamlessly to the eat-in kitchen and out to the deck for easy indoor-outdoor living. The spacious kitchen includes stainless steel appliances, center island, custom countertops, backsplash and breakfast nook. The second level includes a primary suite with walk-in closets and a jetted tub, plus 3 additional bedrooms. A renovated hall bathroom, an abundance of storage, permanent attic stairs and a 2-car garage add everyday ease. The large, fenced backyard and storage shed handle the rest. Minutes to I-64, Bypass-168, Greenbrier dining, shopping, ice skating and more.

1026 Woodwind Way, South Chesapeake

4501 Overlook Pl, West Chesapeake
$585,000
4 Beds ⋅ 3 Baths ⋅ 10623896 MLS
Welcome to this spacious 4-bedroom, 3-bath home featuring a bright and open floor plan designed for comfortable living and entertaining. The beautiful kitchen offers abundant cabinet space, stainless steel appliances, granite countertops, and a large center island perfect for gatherings. The first floor includes a generous family room, office area, and additional living space, providing flexibility for work and relaxation. Upstairs you’ll find 4 generously sized bedrooms with ample closet space. The primary suite features both a walk-in closet and an additional closet, along with a private bath with dual vanities, jetted tub and nice size shower. Recent updates include all new carpet and a new tankless gas water heater. Step outside to enjoy the fenced backyard, while the home’s location on a quiet end street offers extra open space nearby for play and outdoor activities. Located in the desirable Western Branch area, this home provides comfort, space, and a peaceful community setting.

4501 Overlook Pl, West Chesapeake

355 Middleton Way, South Chesapeake
$582,500
4 Beds ⋅ 2.1 Baths ⋅ 10635073 MLS
Welcome to resort-style living in highly sought-after Hickory Manor! Beautifully maintained and showing like brand new, this stunning home offers the perfect blend of modern comfort and style. The bright, open-concept living spaces are highlighted by a showstopping kitchen featuring upgraded cabinets, premium countertops, and a custom backsplash added after the original build. Beyond the pristine, move-in-ready interior, you will enjoy a low-maintenance lifestyle with unparalleled HOA amenities that are truly one-of-a-kind in Hickory. Enjoy worry-free living with grounds maintenance and trash pickup included. Spend weekends at the resort-style pool with its outdoor kitchen and cabana, hit the 24/7 fitness center, or host parties in the expansive clubhouse great room. The neighborhood boasts scenic trails, 5 community lakes, a playground, and vibrant monthly community events. Schedule your tour today!

355 Middleton Way, South Chesapeake

620 Spurlock Way, South Chesapeake
$582,500
4 Beds ⋅ 3 Baths ⋅ 10630505 MLS
Tucked away on a quiet cul-de-sac, this beautiful brick ranch offers the lifestyle buyers are searching for in a setting that feels both private and welcoming. Inside, a flowing layout greets you with built ins at the entry, a dining space, and a stunning living room with vaulted ceilings, skylights that fill the space with natural light, & a brick wood burning fireplace. The kitchen is designed for gathering with a tiered island, granite countertops, stainless steel appliances, and a walk in pantry. The finished room over the garage with cherry wood floors offers flexible space for a media room, playroom, or office. The bedroom wing features fresh carpet, two guest rooms, & a spacious primary suite where you can wake up overlooking the pool, enjoy your morning coffee from the window seat, and step directly onto the back deck. Outside, a tree lined backyard creates the perfect space to relax or entertain, with an extended concrete pad for your boat just in time for summer on the water.

620 Spurlock Way, South Chesapeake

605 Foxgate Quarter, South Chesapeake
$582,000
5 Beds ⋅ 3 Baths ⋅ 10637811 MLS
One owner home which was custom designed and built in 1991. Situated in the heart of Great Bridge. 5 bedrooms, (1 downstairs is currently used as an office). 3 full baths, downstairs bath has ceramic tile and a shower. Primary bath was remodeled in 2024. Manufactured Hardwood floors were installed in the den and foyer in 2021 and in the LR, DR, and Kitchen in 2016. The Den has a cathedral ceiling, 2 skylights, a gas FP, built in cabinets and has a pass thru from the kitchen. Stainless steel appliances installed in 2018. There is a gorgeous and peaceful screened in back porch and a brick paver patio. Painted custom crown molding throughout the downstairs. A new concrete driveway and sidewalk was poured in 2021. Back yard is fenced but three different sections are owned by the 3 neighbors.

605 Foxgate Quarter, South Chesapeake

1937 Flintshire Drive, South Chesapeake
$580,000
4 Beds ⋅ 2.1 Baths ⋅ 10641398 MLS
Welcome to Summer Park at Parkview! This spacious 4-bedroom, 2.5-bath home offers a bright, open layout with a soaring two-story foyer, 10-foot ceilings, and inviting living spaces designed for everyday comfort. The eat-in kitchen features stainless steel appliances, a center island, pantry, and opens seamlessly to the family room with a cozy propane fireplace. Upstairs, the spacious primary suite offers a vaulted ceiling, oversized walk-in closet, and an ensuite bath with dual vanities, a garden tub, and separate shower. Thoughtful updates include luxury vinyl plank flooring throughout the first floor and new stair carpeting (2024), newer refrigerator, dishwasher, and double oven, plus a brand-new high-lift garage door with LiftMaster wall-mounted opener installed in 2026. Step outside to enjoy the composite Trex deck overlooking the backyard, professionally designed landscaping with drainage improvements, and a 10x16 shed with electricity—perfect for storage, hobbies, or a future workshop. Located in the desirable Grassfield school district with neighborhood playgrounds, nearby parks, and convenient access to shopping, dining, and major roadways. Schedule your showing today! Incentives may be available through preferred partners. Contact listing agent for details and eligibility.

1937 Flintshire Drive, South Chesapeake

1537 Waterway Circle, South Chesapeake
$580,000
3 Beds ⋅ 3 Baths ⋅ 10641081 MLS
Enjoy low-maintenance living in this beautifully updated brick ranch with vinyl-wrapped soffits and fascia, plus oversized gutters and downspouts. The open-concept layout is filled with natural light and features 3 bedrooms, 3 updated baths with custom tile, modern vanities, and upgraded fixtures. A private third bedroom offers an ideal in-law suite or student retreat. Flexible living spaces include a first-floor bonus room perfect for an office, playroom, or hobby room, plus a finished room over the garage with a closet and window that can serve as a fourth bedroom. The upgraded kitchen showcases newer cabinetry with lighting, quartz countertops, and updated appliances. A breakfast bar overlooks the sunken great room, creating the perfect space for entertaining. Located in the sought-after Hickory/Butts Road school district with easy access to the Great Bridge Bypass and major interstates. A rare find that won't last long!

1537 Waterway Circle, South Chesapeake

504 Bonsack Court, South Chesapeake
$580,000
4 Beds ⋅ 2 Baths ⋅ 10638636 MLS
Check out this cream puff! Beautifully maintained and thoughtfully updated, this standout home in sought-after Pines of Warrick is ready to impress. Situated on an oversized lot, the backyard is an entertainer's dream with a sparkling in-ground pool and plenty of space to relax and unwind. Gorgeous hardwood floors flow throughout the first floor. The expanded primary suite features two closets and a beautifully updated bath with dual vanities, a walk-in shower, and oversized soaking tub. Updated kitchen and baths offer timeless appeal. The FROG provides a flexible fourth bedroom, office, or media room, while abundant storage includes a floored attic. Meticulously maintained and move-in ready, this is the one you've been waiting for in Great Bridge!

504 Bonsack Court, South Chesapeake

776 Big Bear Lane, South Chesapeake
$580,000
4 Beds ⋅ 2.1 Baths ⋅ 10638907 MLS
$10,000 IN CLOSING COST ASSISTANCE OFFERED - use it to lower your interest rate or reduce your cash to close! Built in 2022 and move-in ready, this meticulously maintained Culpepper Landing home offers modern finishes and an open-concept layout. The gourmet kitchen features quartz countertops, a large island with seating, gas cooktop, double ovens, stainless steel appliances, under-cabinet lighting, walk-in pantry, and breakfast area. The family room features a gas fireplace with granite surround. LVP flooring, a private office, and drop zone complete the main level. Upstairs, the spacious primary suite includes a sitting area, two walk-in closets, double vanity, and Roman shower. Three additional bedrooms, a full bath, and laundry room with utility sink provide plenty of space. Enjoy the covered patio, tankless water heater, and two-car garage. Community amenities include a pool, playgrounds, dog park, golf-cart-friendly streets, and year-round events. Schedule your showing today!

776 Big Bear Lane, South Chesapeake

504 Sydenham Boulevard, South Chesapeake
$580,000
4 Beds ⋅ 2.1 Baths ⋅ 10634574 MLS
Beautifully redone and move in ready, this home blends updated finishes with functional living throughout. The first floor features durable LVP flooring and a recently renovated kitchen with quartz countertops, open shelving, farmhouse sink, LG stainless steel appliances, and a spacious walk in pantry. Custom trim details, shiplap accents, wainscoting, and dining room molding add character and charm throughout the home. Bathrooms have also been recently updated for a fresh, modern feel. Upstairs offers generously sized bedrooms with plenty of space to spread out. Enjoy the backyard oasis featuring a saltwater pool, pergola, playhouse, a chicken coop, and recently expanded concrete patio space perfect for entertaining and relaxing. Conveniently located near Edinburgh Shopping Center, grocery stores, dining, and everyday conveniences. An assumable loan with a rare 2.99% interest rate may also be available for qualified buyers.

504 Sydenham Boulevard, South Chesapeake

Some listings may be duplicated in the search results due to the co-mingling of listings from more than one multiple listing service. Should there be different listing information between the duplicated listings; user is advised to verify the accuracy of the listing information before making any financial decisions.